The study aimed at the relationship between planning skills and entrepreneurial performance of small-scale enterprises in Kyengera town council. The target population for the study encompassed all formally registered small business owners in Kyengera Town Council who had less than 50 employees and had been operational for at least two years. These parameters were applied to ensure the selected owners had adequate experience to reflect on the level of planning skills employed as well as business performance achieved over time. Using purposive sampling techniques that involved consulting with trade associations and local government authorities, the researcher was able to identify and select a total of 120 entrepreneurs representing various sectors such as apparel, food processing, furniture making, retail services and welding works to participate in the study. There was a positive high significant associative relationship between planning skills and performance of Small-scale enterprises in Kyengera Town Council. (r = 0.688, Sig= 0.000). The positive high correlation implied that the positive change in planning skills led to a positive change in performance of Small-scale enterprises in Kyengera Town Council and vice versa. Therefore, null hypothesis, which stated that “There was a no relationship between Planning skills and performance of Small-scale enterprises”, was rejected and the Alternative hypothesis which stated that, “There was a relationship between planning skills and performance of Small-scale enterprises” was accepted. The study recommends that SMEs in all sectors in Uganda should enhance managerial planning skills as a tool and a concept to be used in improving organizational performance. This is because once the level of problem analysis is improved, accuracy in forecasting and goal setting is enhanced among SMEs then profitability is achieved, as well as product quality and hence sales growth.